1199631-29-2

Basic information

• Product Name: (S)-3,3'-bis(4-Methoxyphenyl)-[1,1'-Binaphthalene]-2,2'-diol
• Synonyms: (S)-3,3'-bis(4-Methoxyphenyl)-[1,1'-Binaphthalene]-2,2'-diol;(S)-3,3'-Bis(4-methoxyphenyl)-[1,1'-binaphthalene]-2,2'- diol, 99%e.e.
• CAS NO: 1199631-29-2
• Molecular Formula: C34H26O4
• Molecular Weight: 498.56784
• Mol File: 1199631-29-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 624.7±55.0 °C(Predicted)
• Appearance: /
• Density: 1.251±0.06 g/cm3(Predicted)
• PKA: 8.20±0.50(Predicted)
• CAS DataBase Reference: (S)-3,3'-bis(4-Methoxyphenyl)-[1,1'-Binaphthalene]-2,2'-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3,3'-bis(4-Methoxyphenyl)-[1,1'-Binaphthalene]-2,2'-diol(1199631-29-2)
• EPA Substance Registry System: (S)-3,3'-bis(4-Methoxyphenyl)-[1,1'-Binaphthalene]-2,2'-diol(1199631-29-2)

Safety Data

• Hazardous Substances Data: 1199631-29-2(Hazardous Substances Data)

Usage

General Description

(S)-3,3'-bis(4-Methoxyphenyl)-[1,1'-Binaphthalene]-2,2'-diol, also known as (S)-BINOL, is a chiral compound with two naphthol groups. It is widely used as a ligand in asymmetric synthesis and catalysis due to its ability to form complexes with various metals. Its chiral nature makes it an important reagent in the production of enantiomerically pure compounds. Additionally, (S)-BINOL has been studied for its potential antioxidant and anti-inflammatory properties, making it a subject of interest in the pharmaceutical and medical research fields. Overall, (S)-BINOL is a versatile compound with applications in both chemical synthesis and biomedical research.

Upstream product

• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
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• 189518-78-3 (Ra)-3,3’-diiodo-2,2’-bis(methoxymethoxy)-1,1’-binaphthalene 
• 602-09-5 1,1'-bi-2-naphthol 
• 142010-87-5 (±)?3,3'?dibromo?2,2'?bis(methoxymethyl)?1,1'?binaphthalene 
• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 
• 756491-45-9 (+/-)-3,3'-bis(4-methoxyphenyl)-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 
• 5720-07-0 4-methoxyphenylboronic acid 
• 171364-79-7 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant articles and documents

Chiral Bronsted acid catalyzed enantioselective Mannich-type reaction

Mannich-type reaction of ketene silyl acetals with aldimines proceeded catalytically by means of a phosphoric acid diester, derived from (R)-BINOL, as a chiral Bronsted acid to afford β-amino esters with good diastereoselectivity in favor of the syn isomer and high enantioselectivity (up to 96% ee). The highest enantioselectivity was achieved by the phosphoric acid diester bearing 4-nitrophenyl groups on the 3,3′-positions of BINOL. The N-2-hydroxyphenyl group of aldimine was found to be essential for the present Mannich-type reaction. In combination with these experimental investigations, two possible monocoordination and dicoordination pathways were explored using density functional theory calculations (BHandHLYP/6-31G*). The present reaction proceeds via a dicoordination pathway through the zwitterionic and nine-membered cyclic transition state (TS) consisting of the aldimine and the phosphoric acid. The re-facial selectivity was also well-rationalized theoretically. The nine-membered cyclic structure and aromatic stacking interaction between the 4-nitrophenyl group and N-aryl group would fix the geometry of aldimine on the transition state, and the si-facial attacking TS is less favored by the steric hindrance of the 3,3′-aryl substituents.

Expedient BINOL derivative arylations

A dramatic improvement of our previous methodology based on a Suzuki-Miyaura cross-coupling to access 3,3′-disubstituted H8-BINOLs using microwave heating is reported herein. These new conditions represent a large gain in term of atom-economy, reaction time, catalyst loading, and excess of reagents employed.

Photocatalyzed E→Z Contra-thermodynamic Isomerization of Vinyl Boronates with Binaphthol

The photocatalytic contra-thermodynamic E→Z isomerization of vinyl boronates by using a binaphthol catalyst is disclosed. The reaction, based on the transient formation of a suitable chromophore with a BINOL derivative as the catalyst, allowed geometrical isomerization in good-to-excellent Z/E ratio and excellent-to-quantitative yields. The mechanism of this E→Z contra-thermodynamic isomerization was studied, and the formation of a transient chromophore species is suggested.